His Daisy
by darkheadlights
Summary: If Jess hadn't run away to California and had taken Rory to the Stars Hollow High prom, like he was supposed to. Literati. Told (mostly) from Jess' perspective. Separate universe from Puzzle Pieces. Rated T for language (Jess has a dirty mouth).
1. You Can't Promenade Alone

**A/N:** **To my ****_Puzzle Pieces_**** readers – don't worry! I'm still working on that one too! This idea just popped into my head, so I had to get at least some of it out before I forgot it. Keep reading! :)**

**P.S. If you've never read The Great Gatsby, 1. It is a great book. Go read it now. 2. There are spoilers to that book in this story, so proceed cautiously! **

_I can't believe I'm doing this_, Jess mentally groaned as he stood in line to buy tickets to prom. From the very first time he'd even heard of such a thing as a "prom," when he was seven years old and his older next-door neighbor was taking his girlfriend, Jess had thought "Prom means you dress up in a silly outfit and take a girl in an even sillier outfit to dance with a bunch of other kids in silly outfits? What's the point?" Here he was, ten years later, doing something he had sworn long ago never to do. _It's for Rory_, he chided himself silently and softening a little. Rory. She was special. He would never, _ever _say that out loud, to _anyone_. But she was. He had once thought she didn't give a damn about him. The ridiculous town dance marathon changed all that.

_"So…you're broken up with Dean?" Jess asked, standing on the dock and looking down at Rory, who looked like she'd stepped out of the pages of a 1950s LIFE magazine. She glanced up. Her bright blue eyes were huge and still damp with tears._

_"I'm broken up with Dean," she confirmed._

_"Okay," he said simply, and walked away. Time to say goodbye to Shane…whatever her last name was. He glanced over his shoulder just once, and Rory was gazing after him, looking confused. They'd figure it out._

And they had. They had a somewhat tumultuous relationship, sure, but unless you were a pod person, or didn't even care about each other (like him and Shane), that was pretty normal.

"Hey. Hey!" Someone was shouting at him, shaking him out of his own thoughts.

"What?" he snapped.

"Do you want a ticket, or what?" He suddenly found himself at the head of the line. People behind him were shuffling and complaining. Apparently he'd just been standing there, motionless, for at least a minute or two.

"Yes, obviously I want a ticket. I was standing in the ticket line, wasn't I?" Jess shot back to the girl who had yelled at him. She rolled her eyes.

"How many?"

"Two," he told her. She squinted at him suspiciously. Apparently she didn't buy that anyone would want to go to prom with him. "I'm taking my grandma," he said, just to have a little fun and make his already-terrible reputation here even worse. Hey, he was gonna be out of here any day now. He'd just barely scraped by with his grades. One more F, one more detention, and he wouldn't have graduated. _They could still stop me from graduating_, he suddenly realized. _Oh shit_.

"Sorry," said Jess quickly to the ticket-selling girl, and put on his best shit-eating grin. "I guess I spaced out there for a sec. I'm taking my girlfriend, so I need two." A long pause. He sighed. "Please." She quit squinting at him and handed him two tickets.

"That'll be forty dollars, please," she said, acting much nicer than a moment ago. _People are so easy to manipulate_, Jess thought. _And forty dollars? What a rip-off_. He forked over the cash and took the tickets, which resided in a small folder with a familiar-looking illustration on the cover. He frowned at it.

"What's the theme this year?" Jess asked.

"_The Great Gatsby_," the girl replied, rolling her eyes again. "I don't know whose bright idea that was. Probably some teacher." Jess smiled, a real one this time. Maybe this wouldn't be so bad.

"So, I got the tickets," Jess said a few hours later, sitting across from Rory at Luke's. She gave him a brilliant smile. He tried to pretend it didn't affect him like it did.

"The prom tickets?" she asked excitedly. He nodded. "Yay!" She stood up, nearly knocking over her chair, and wrapped him in a bear hug.

"Jeez!" he exclaimed, but it was in a good-natured way. Rory touching him could never be truly annoying. Unless she was repeatedly poking him, which she occasionally did when she was bored at the movies.

"Oh, I'm so excited," Rory said, taking her seat again and waving an apology at Luke, who was glaring at her from behind the counter. Lorelai was there too, picking reluctantly at a grapefruit Luke had set before her. She'd already eaten the maraschino cherry that came in the middle. "Thanks, Jess. I know this is the last thing you want to do with your Saturday night."

"Well, hey, maybe it won't be so bad," Jess shrugged. "The theme is _The Great Gatsby_." Rory really did knock over her chair this time in her haste to get to her mom.

"Mom! Mom!" Rory yelled. "The prom's theme is _The Great Gatsby_!" Lorelai looked a little taken aback by her daughter's excitement, but relaxed as soon as she knew why Rory was freaking out. Then a gleam glinted in her eye.

"Can I make your dress again?" Lorelai asked, looking like she was already mentally sifting through fabric options.

"Yes!" Rory shouted. Luke looked like he was about to have an aneurysm from all the shouting. Lorelai leapt up from her stool and the two Gilmore girls started jumping up and down and squealing. Jess hunched down in his leather jacket, trying to pretend to be somewhere, anywhere else. Luke pointedly slipped in the back room, holding his hands over his ears. After a minute or two, completely oblivious to all the nasty looks they were getting from other diners, Lorelai and Rory stopped jumping and squealing and Rory turned her chair the right way around.

"You can be Gatsby and I'll be Daisy!" she exclaimed to Jess, who was still hunched down, trying to make himself invisible.

"Great, so you'll leave town with some other guy and I'll end up face-down in a pool," Jess said. Rory waved away his sarcasm.

"It's gonna be great," she said happily, finally tucking into her burger and fries. Jess smiled. Maybe it would be.

**A/N: Please review and let me know what you think so far! I never liked that Rory didn't get to go to prom. I hated my own prom, to be honest, and would love a chance to do it all over again. I'll just live vicariously through Jess and Rory. ;)**


	2. Sparkles and Suits

**A/N: The dress I picture Rory wearing is inspired by the upcoming Baz Luhrmann adaptation of ****_The Great Gatsby_****, which I'm really excited for. I saw a screenshot of Carey Mulligan wearing this fabulous pink dress. I changed it a little for the story – I don't want to rip off the costume designer completely – but if you want to picture Rory in her dress, Google the upcoming movie and take a look. :)**

**Also, I know a lot of people say that fedoras are douchebag hats nowadays, but let's be real – if anyone can pull off a fedora, it's Jess Mariano.**

"This is too sparkly," Rory complained, craning her neck to check the reflection of the back of the dress she had on.

"It is not too sparkly," Lorelai countered. "It's just sparkly enough. The Roaring Twenties were sparkly!" Rory shrugged and turned to face the full-length mirror set up in the living room again.

Lorelai had truly outdone herself this time. Rory's dress for the Chilton dance had been amazing, but because this was prom, and a once-in-a-lifetime experience, Lorelai had pulled out all the stops. The dress fell to just above Rory's knees. It was sleeveless, palest pink, and, as Rory said, extremely sparkly, thanks to the fabric Lorelai found at a shop in Hartford. It clung tight to her chest and stomach but fell straight down from the hips on. Not many girls could pull off a dress like this. Only someone with a perfect flapper figure would look good in it. The neckline was high – Rory was a modest girl, whose style wasn't quite as sexy as Lorelai's, at least not yet, which Lorelai was actually thankful for – but it dipped down low in the back, exposing Rory's shoulder blades and mid-back. Despite her protests, Lorelai could see that Rory couldn't take her eyes off herself.

"Mom, it's – it's amazing," Rory said, shrugging and smiling. "It's _really _sparkly, but I guess you're right – the twenties were sparkly."

"All that glitz and glamour hid all the dirty stuff that was going on behind closed doors," Lorelai added, giving Rory a wink.

"Actually, that's true," Rory said, going into scholar-mode. "F. Scott Fitzgerald was rumored to be quite the ladies' man. And he and Zelda drank _all _the time. Of course, everybody did in those days. The twenties weren't as glamorous as everyone thinks they were," Rory finished, looking at her mom's face in the mirror's reflection. Lorelai grimaced.

"Well, hopefully my little girl won't be drinking and messing around for at _least _another decade," Lorelai said with a long-suffering look on her face. "Preferably three decades. Or four. I'm more comfortable with four; let's leave it there." Rory grinned.

"Don't worry, Mom," Rory said, turning to give her mom a careful hug – there were still pins in the dress. "I'm not a troublemaker."

"I know, hon. I trust you. It's Jess I don't – " Lorelai stopped. Rory was giving her a glare, or, at least, the closest thing to a glare Rory could achieve. "All right, all right," Lorelai conceded, backing off. "I'll say no more." Rory looked relieved. "Ooh! But can I call him Tess when he comes to pick you up?" Rory rolled her eyes.

"Okay, but you do so at your own risk. I'm not responsible for any damages to your person," she said. Lorelai pouted.

"Whatever you say, Cory!" she said in a singsong voice and pranced into the kitchen to make coffee. Rory couldn't help but giggle after her.

"Mom! The pins!" she shouted as she shuffled carefully after Lorelai.

Miles away, Jess was reluctantly sifting through various suits at a hole-in-the-wall thrift shop. A very elderly Italian man, the owner, was standing close behind him. He would burst out with random information about the suit Jess happened to have his hand upon at any given moment. Luke stood in the corner, looking at mothball-scented ties and smirking. He knew full well that the only person in the world who could get his nephew to buy a suit was Rory.

"What about this grey one?" the man said hopefully, pulling out a slim-cut, dove-grey suit. Jess looked at it appraisingly. So did Luke, even though he knew about as much about suit-buying as Jess did. _Too bad Lorelai isn't here to help_, he thought. _She'd find the perfect thing in two seconds flat, and probably haggle it down from full price too_.

"That looks good, Jess," Luke said. Jess gave him a death glare. "Sorry, sorry," said Luke, holding up his hands. "I won't say another word." Jess turned back to the suit the old man was still holding up.

"I'll try it on," he said, sounding about as enthusiastic as someone who was about to get a colonoscopy. Secretly, though, he couldn't help feeling the _tiniest _bit excited, which he would never, ever admit to Luke or anybody else. Even though Jess wasn't the elder Lorelai's biggest fan in the world (Luke took that honor), he knew she was a skilled seamstress and would make something spectacular for Rory to wear. Trying to look like he actually deserved to be standing next to her was the least he could do. The old man scurried after Jess as he strode to the back of the store, where the changing rooms were. "I can take it from here," he said, taking the suit. The man was so attentive Jess was a little concerned he was going to follow him into the changing room, but he backed away, bowing slightly. Jess whipped the curtain closed and stripped off his jeans.

A few minutes later, Jess reluctantly emerged. Somewhat illogically, there wasn't a mirror inside the fitting room. The suit felt pretty good – not that Jess really knew what a suit was supposed to feel like, never having tried on one before – but he knew he had to look at it too.

"Ohh, _perfetto_!" exclaimed the Italian owner, clapping his hands when he saw Jess walk out. "_Magnifico_!" Jess scowled, but then he saw his reflection in the full-length mirror, propped up against one of the store's columns. He couldn't hide his shocked expression. He actually looked…pretty damn good, if he did say so himself. He'd been expecting the suit to be way too big, or at least the pantlegs to be too long – he wasn't the _tallest _of guys, though he made up for that in attitude ("The bigger you are, the more space there is for stupid," is what he always said about Stars Hollow High's football players – and Dean). But the suit was a perfect fit, just like the owner said. Even the jacket fit just right. He'd been expecting the shoulders to be too broad.

Luke didn't say anything, as promised, but Jess could see in a glance that he thought the suit looked pretty decent too.

"This is for twenties dance, no?" the owner inquired. Jess nodded. "You look just like that," the man assured him. "Just like twenties." He gasped. "A hat! You need a fedora!" Jess' eyes widened. He hadn't bargained on a _hat_. He didn't even wear baseball caps. Maybe a skullcap, if it was really cold out. Before he could say anything, though, the man rushed over with a matching dove-grey fedora and plopped it on Jess' head. A movement in the corner caught his eye and he turned to see Luke's shoulders shaking as he tried to contain his laughter.

"Okay, maybe not the hat…" Jess said firmly, pushing it into the owner's hands, who pushed right back.

"I throw it in for free with the suit," he said just as firmly. Jess shrugged. Hey, if it was free, why not? He could always pass it off on somebody else. He turned heel and went back into the dressing room to put his jeans back on.

"Hey, Jess, think you'll be able to find a nice button-down and a tie at Walmart?" Luke called after him, still laughing about the fedora. If Jess could have slammed the curtain closed behind him, he would have.

"I'll get one at – whatever clothing store they've got around here," Jess called back grouchily. The suit he needed to get used, but he could afford a new shirt and a tie, especially with the extra cash he was making at…yes, Walmart. Sometimes he still couldn't believe he worked there. But it was paying for this stuff, and he could definitely afford to get a corsage or whatever crap he was supposed to get for Rory. Reemerging, Jess paid for the suit and fedora and threw them in the passenger seat of Luke's pickup. "I'll be back later," he muttered to Luke. "Hang up that suit for me, will ya?"

"Where are you going?" Luke asked, even though he knew there was usually about a two percent chance of Jess actually telling him.

"Out," Jess called, already striding away and pulling out the book he had in his back pocket. It was _The Great Gatsby_. He wanted to refresh his memory.

**A/N: Please review!**


	3. My Fair Fonzie

**A/N: I never liked that Lane didn't get to go to prom with Dave, same as I didn't like that Rory didn't get to go at all. So, I'm 'fixing' that. All apologies for messing with your universe, Amy Sherman-Palladino. Please forgive me. All credit for the creation of this wonderful, weird universe goes to you.**

"This is gonna be so much better than the Chilton prom," Rory said happily as she and Jess walked hand-in-hand around Stars Hollow. "Their theme is 'Reach for the Stars!'" She rolled her eyes and Jess snorted.

"How original," he said sarcastically.

"I know, right? _The Great Gatsby_ is a _great _theme. I can't wait. One more week!" She did an impromptu little dance, still holding Jess' hand. A smile quirked its way onto his face at his girlfriend's crazy behavior. "They do get the Wadsworth Mansion, though," she added, looking a little disappointed. "I mean, I was all against it, but now I really wish – well, I'm sure the Stars Hollow High gym will be just fine." She still looked uncertain, though.

"Hey, are you expecting to dance at this thing?" he asked her, voicing a concern that had been on his mind ever since Luke asked him whether he'd picked up 'dancing shoes' at Walmart yet (Luke tended to hang onto a subject when he thought it was funny). Jess had to admit, picturing himself dancing was not only humiliating, but also pretty funny, which meant he definitely wouldn't be displaying that particular non-talent in any public forums anytime soon.

"Um…kinda. But no fast dances, unless it's Bowie or something," Rory said. "One slow dance? Maybe two? Please?" She gave him puppy dog eyes, which he tried and failed to resist.

"_One _dance," Jess said firmly. "_Maybe _a fast dance. If it's Bowie. And if you're really, really lucky." Rory grinned.

"I am!" she said, happily clinging to her boyfriend's arm. Jess smiled again. He seemed to be doing a lot more of that ever since he and Rory got together. He hated to admit it, but she was a good influence on his normally-stormy demeanor.

"What's your dress like?" Jess asked as they strolled around the gazebo. Rory gave him a Look.

"Jess, you know I can't tell you that," she scolded.

"What, it's not like we're getting _married_. I can hear about the dress," he retorted. She shrugged.

"Well, I'm not telling you. It'll be a surprise."

"You do realize I have to buy you one of those dumb corsages, right?" he said. "So I at least need to know the color."

"Pink," Rory conceded. "But that's all I'm telling you."

"Can you tell me if I'll like it?" Jess asked, squeezing her hand. Rory laughed.

"Oh, I think you'll like it," she assured him, kissing him on the cheek. Jess turned his head so the kiss would land on his lips instead.

"No fair," Rory pouted, but leaned in for another kiss. Jess wrapped his arms around her like he had the first time they'd really kissed, out on the street near that payphone. Luke's apartment didn't count, at least not to Jess. He pulled back for a minute and opened his eyes, catching a glimpse of someone staring at them from across the street. It was Dean, Doose's apron in hand. Jess placed his arm around Rory protectively and steered her towards Kim's Antiques so she wouldn't see her ex-boyfriend. He had a sinking feeling that Dean was going to prom as well, and most likely wasn't going to let sleeping dogs lie.

"So what does your suit look like?" Rory asked, hopeful that her boyfriend wasn't going to try to take her to prom in his usual jeans and leather jacket. His style didn't bother her at all normally, but it was more _Happy Days _than _Gatsby_. Rory snorted at the thought of Jess as the Fonz, whacking a jukebox to start it and saying "Ayyyy!"

"What, are you picturing me in a suit?" Jess asked, mock-insulted at Rory's snort.

"No, no," she assured him. "Um…just thinking about what happened to Taylor yesterday. Random! But tell me about your suit," she said insistently. Jess smiled.

"You'll like it," he said simply.

"Oh, come on, you at least have to tell me the color. I gave you that much," she pointed out.

"Grey," Jess told her. Rory mused over that.

"That could work."

"I guess we'll find out," Jess said.

"I guess we will," Rory agreed, smiling.

"Rory!" someone yelled, and suddenly a petite Korean girl was barreling into them, pushing Rory right out of Jess' grasp. "Sorry, Jess!" Lane apologized, blushing a little. She never seemed to feel completely comfortable around him, he had noticed.

"Hi, Lane!" Rory said. "You seem chipper." Lane started hopping up and down, proving just how chipper she was, as Jess backed away slightly to give her hopping space.

"I'm going to prom!" Lane exclaimed. "With Dave!"

"Oh my god!" Rory said, starting to bounce a little herself. "Really? Mrs. Kim said yes?" Lane nodded, a huge smile on her face.

"Mrs. Kim said yes," she confirmed. "It's a minor miracle. Of course, I have to go to Bible camp again and help out twice as often around the store and my mom has to approve of my dress _and _I have to keep the 'Holy Spirit'" – here Lane made quotes with her fingers and rolled her eyes – "between me and Dave while we're dancing, but my mom's not _going _to prom, so she won't be able to see, will she?" Lane suddenly looked very concerned. "Wait, I have to go check and make sure she's not going to prom. Bye, Rory! Bye, Jess!" she yelled as she ran away, disappearing as quickly as she had appeared. Rory laughed at her best friend's antics and she and Jess resumed their walk around the square.

"This prom is going to be _so _great," she gushed, even happier than she'd been a few moments ago, now that she knew her best friend got to go. Jess said nothing, but he smiled yet again. He had a little plan in his back pocket. He wasn't sure if he was going to be able to pull it off or not, but if he did, and if he knew Rory (which he did), prom was going to be even better than she imagined. And nobody – not even Dean – was going to interfere with that.

**A/N: I know, I know, I just love to drag Dean into my stories and then shove him right back out. He'll make another appearance, mark my words. I like to toy with him the way a cat likes to toy with a mouse. *evil grin* Hey, there's gotta be ****_some _****drama in this story; it can't be all perfect happy Literatiland all the time. *sigh* And apparently I like to start out with one POV and then switch into another, then switch back…bad writing habits. Sorry about that. Keep reviewing! It keeps me going!**


	4. Rebel with a Cause

**A/N: Read! Review!**

Monday morning, Jess pushed his way into the sweaty-smelling halls of Stars Hollow High, late as usual. Even though he was aware that they could technically still keep him from graduating, he couldn't help himself – he had to push the envelope. Sure enough, Principal Merton came stomping around the corner just as Jess let the doors slam behind him.

"Ah, Jess Mariano," he said calmly. "Who else?" Jess shrugged.

"Were you expecting someone else?" _Stop it_, he internally demanded. _Don't get expelled_. "I mean, yes, sir." The _sir _pained him, it physically pained him, but Principal Merton raised his eyebrows, looking surprised – and pleased.

"Now that's more like it," he said, gesturing for Jess to follow him. "I've given you a lot of slack here, Jess. I know you don't believe that" – he hadn't even turned to see the skeptical expression on Jess' face – "but I have. Now, it would be _painfully _easy for me to tell you that you're not graduating in two weeks. Fun, even. However, I took an oath when I became a teacher that I would never let a smart, worthy student slip between the cracks. And, unfortunately for me, you are smart. And worthy. I think." He sounded uncertain. Jess tried to keep his face neutral. He'd just been expecting another detention that he would, of course, skip out on.

Principal Merton continued: "So, Jess Mariano, I have come up with an adequate punishment for your constant tardiness." _Oh_, Jess thought sullenly, _so I am getting a detention_. "Prom is this week, you know. Are you going?" Startled by this seemingly irrelevant question, Jess didn't answer for a moment.

"Uh, um, yes, I'm going," he said once he'd recovered. Principal Merton nodded. They were standing outside the gym.

"Well, you'll have an even bigger part in it than you expected." Confused, Jess looked past the principal into the gymnasium. About a dozen students were in there, gathering materials and fetching scissors, tape, and glue.

"An art project?" Jess asked. Principal Merton laughed.

"Well, sort of. You're going to help the prom-planning committee set up for Saturday," he said, somewhat gleefully. Jess' knee-jerk reaction was anger – how dare he force him to do something dumb like this? He'd take the detention over this any day. But the quick burst of fury was gone as quickly as it had come. He realized this unexpected turn of events could actually help him. He smirked.

"Sure thing, Princi-PAL Merton," Jess said, unable to resist the little jab. But the principal looked too taken aback at Jess' agreeableness to notice.

"Uh – well – okay then. You have permission to skip your first class. As long as you help out these guys," he said, indicating the students in the gym. Jess nodded, and Principal Merton walked away, looking a little dazed.

Jess wandered into the gym, glancing around at the other students there. He knew all of them by sight but had never paid enough attention to learn their names. A girl came up to him.

"Hey, are you Jess?" she asked. He realized it was the same girl who had sold him the prom tickets a few days ago.

"That's me," he said drily. She nodded.

"Hey. I'm Sandy. So. Here's what we're working on." Sandy led him over to a pile of fake pearls. "These are all tangled up. We want to hand them out to everyone as they come in, so we need someone to untangle them." She looked at Jess expectantly. _Really? _he was thinking. But he had to remember his plan. He took a deep breath and _shoosh_ed it out. _Rory_, he thought. _Rory_.

"Sure," he said, smiling tightly. He set to work.

An hour later, the necklaces were neatly organized and Jess felt like his brain was going to combust from the pure monotony of it all. He turned to Sandy, who was painting a banner a few yards away. "Hey," he called. "I'm done." She looked over.

"Good job! I guess you should head to your next class. In fact, we all should," she said, glancing at her watch. Jess stood and shuffled over.

"Hey, uh…I was wondering." Sandy looked at Jess expectantly. He entered suck-up mode. "This is gonna be our only prom, you know? Then we're all going off to college, or – wherever, and it's the last hurrah before graduation."

"Uh-huh," Sandy said slowly.

Jess continued, "So I was thinking. Why let this prom be just as lame and boring as every other prom out there? I was rereading _Gatsby_ – " Sandy looked confused all of a sudden. "The book the prom is based on?" Her face cleared.

"Oh right," she said. It took everything Jess had not to roll his eyes.

"I was rereading _Gatsby_ and all the parties they have in the book are these lavish, indulgent, expensive affairs. I was just hoping our prom could be something…better," he finished lamely, seeing that he was losing Sandy's attention.

"That's not a bad idea" said a voice from behind Jess. It was a teacher; Mr. Carraway, if Jess remembered correctly. He taught English. "I like the way you think," he said, looking at Jess.

"You wouldn't say that if you knew me," Jess assured him. Mr. Carraway laughed.

"Let's see if we can't do something about that," he said, looking thoughtful. Jess smiled.

**A/N: A teacher Jess likes?! Unheard of! But I think even the "rebellious" types had their favorite teachers in high school too. I wonder what else Jess has up his sleeve...?**

**P.S. Anyone catch the ****_Gatsby _****reference?**


	5. Pomp and Circumstance

**A/N: This chapter is all about Rory's graduation, so I had to borrow Rory's speech from "Those Are Strings, Pinocchio", the third season finale (except for a small change, which I added). I do not own any of it – I wish I did! Things are mostly the same, except Jess comes to Rory's graduation, like he was supposed to. I didn't borrow much other dialogue, so if it seems different, that's because it is. This chapter doesn't really have anything to do with prom – I just wanted to rewrite the graduation. Teensy bit of JJ as well as the usual Lit.**

It was late Wednesday morning and the Gilmore house was in chaos. Lorelai had, for some reason, decided to bring her entire wardrobe downstairs to pick out the perfect outfit for Rory's graduation, and even though Rory herself knew exactly what she was wearing, she was freaking out about Lorelai's outfit. Jess stood in the middle of it all, feeling a bit like he was in the eye of a hurricane.

"At least I'm not worried about my outfit matching the _grass_, like my mother," Lorelai groused, rolling her eyes.

"At least Grandma knows what she's wearing!" Rory called from her room. Jess awkwardly leaned against the door frame between the entranceway and the kitchen. He was thinking about Jimmy, his father, who had made a sudden appearance a few nights ago. Rory didn't know about the encounter. Jess wasn't sure what to say about it. His father had just sat there in the diner all day long, drinking coffee and not eating anything, and then dropped a huge bomb on Jess, listened to "Suffragette City" with him, and left. Now that Jess knew Jimmy was in California, he kind of wanted to see what more he could find out about the man who'd left before he could even get to know his own son. _Maybe I could take a trip out west while Rory's in Europe_, he mused to himself. His girlfriend shook him out of his thoughts as she came barreling out of her room.

"Did you figure it out yet?" she yelled to Lorelai, even though her mom was standing no less than four feet away. Jess reached out and touched Rory on the shoulder.

"Hey, calm down," he said gently. "This is a great day for you." Jess winced at his sappy words, but the smile on his girlfriend's face was worth the saccharine sentiment. "You look…really good," he added, more softly so only Rory could hear. She blushed.

"Another masterpiece by Lorelai Gilmore," said Rory, giving the pink floral dress a little twirl.

"Well, you wouldn't let me make it any shorter, but it's not half bad," Lorelai said, traipsing into the kitchen to join them. "Jess, I hate to ask you this, but since you're not wigging about what you're going to wear to the ceremony, could you make some coffee?" Jess nodded, secretly grateful to have some kind of purpose in all this. It wasn't like he'd be much help choosing Lorelai's ensemble for the day.

"What about that red lacy dress you just got at the cute place in Hartford?" Rory asked her mother. Lorelai gasped.

"With the matching red cardigan?" she said.

"And your hair down?" Rory said.

"Perfect!" Lorelai cheered, throwing her arms in the air. "Jess, get that coffee going, we need to motor."

"Where are we going?" asked Rory, confused, as Jess dumped grounds into the Gilmores' coffeemaker.

"To Luke's," Lorelai said, as if the answer was obvious.

"Luke has coffee," Rory pointed out.

"I need some for the drive over," Lorelai said, and Rory nodded as if this made sense. Jess didn't question it – he didn't quite understand the devotion to coffee his girlfriend and her mother had, but he knew they were way too far gone to change anything now. Rory had probably developed her addiction to caffeine in the womb.

Ten minutes and three cups of coffee later (one for Rory, two for Lorelai), Lorelai parked the Jeep in front of the diner. The bell rang as they entered. Luke was waiting for them, two cups of coffee already poured for the girls. He was wearing a suit and the ever-present baseball cap was absent from his head.

"Wow," Lorelai said, looking caught off guard. "You look nice." She stared at Luke and Jess covered a smirk with his hand. It was so painfully obvious that Luke and Lorelai were in love, but both of them were in such denial about it.

"You…look great," Luke replied sincerely. He looked awestruck. The two just stared at each other for a beat, while Jess attempted to contain his laughter, then everything sped up again. Lorelai and Rory grabbed their coffees and all four of them sat down at a table.

"Jess, you doing okay?" Luke asked quietly, obviously asking about Jimmy. Jess nodded, glancing at Rory, but she was deep in conversation with her mother.

"I'm fine," he said shortly. This wasn't his day; it was Rory's. He didn't want to ruin it like he had so many other things. Luckily, Luke dropped it. The foursome spent the remainder of the morning and early afternoon at the diner, both of the girls with huge napkins tucked in their collars to avoid spillage.

"We'd better get going," Lorelai said at three. Luke and Jess piled into the green pickup while Lorelai and Rory hopped into the Jeep.

"See you there," Rory called to Jess, waving and beaming. While Luke was in the back with their plates and Lorelai was in the bathroom, she'd told him how happy she was that he was coming to her graduation. Jess shrugged it off, but if he was honest, he was happy too. And Rory had promised to come to the Stars Hollow High graduation the following week. It was the day before she and her mom left for Europe. Jess didn't like the idea of her leaving for so long, but on the other hand, he was still considering going to California to see his dad. He wasn't sure if he was going to tell Rory about it or not.

"Damn," Jess and Luke said in unison as they pulled up to Chilton. It was massive and extremely forbidding-looking. You could mistake it for a prison…albeit a really nicely-built one. Rory and Lorelai parked next to them and Rory shrugged on her gown.

"Do you have a mortarboard?" Jess asked her, smirking. Rory held it up.

"That's why I didn't curl my hair," she said.

"Good thing too; you would have taken even longer to get ready," Jess teased, and she lightly smacked him.

"We'd better go find our seats," Luke said, and Lorelai nodded. "Come on, Jess."

"Just a sec," he called, and waited until the pair had walked a far enough distance away before pulling Rory to him and giving her a deep kiss.

"Mm, what was that for?" she asked when he pulled away.

"Good luck," he replied, and squeezed her hand before following after his uncle.

The friends and family of Rory Gilmore found their seats, Jess purposely sitting as far away as possible from Emily. She still glared at him and muttered "hoodlum" under her breath. _At least I don't have a black eye this time_, Jess thought. He leaned back in his chair and closed his eyes as Luke and Jackson yammered on about the amazing architecture and Sookie constantly got up to take pictures of Rory and sat back down.

"We're not gonna cry during Rory's speech, right?" he heard Sookie say after she'd awkwardly climbed over several strangers.

"Not crying," Lorelai agreed. She reached over and tapped Jackson. "Not crying," she said again. Jackson nodded and repeated the same to Luke, who looked abashed at the thought of tears coming out of his eyes.

"Not crying," he muttered to Jess, who simply stared at his uncle. He couldn't remember the last time he'd cried…well, actually, he could, but no one would ever know about it. A few months ago, Rory had loaned him _Revolutionary Road_, assuring him that it was a great book. She hadn't mentioned how goddamned _sad _it was, and Jess had found himself tearing up not even halfway through it. Luckily, he'd been alone above the diner at the time, so no one ever had to know. When Rory asked what he thought of the book, Jess had just shrugged and said it was good. _Anyway_, he thought, _I'm not gonna cry_ _at this_.

The proceedings soon began, and after a very unique and slightly socialist rendition of the Pledge of Allegiance and a deeply disturbing Broadway tune, Rory came up on stage.

"Whoo!" Lorelai and Sookie both shouted, unabashed by the stares they received. "Go Rory!" Grinning back at all seven of them, Rory began her valedictorian speech. Jess sat up straight and gazed up at her. This was the only part of the graduation he was interested in.

"Headmaster Charleston, faculty members, fellow students, family and friends, welcome. We never thought this day would come…" Rory continued on for a few minutes, thanking her friends and teachers and expressing her deep love for the world of literature – that part made Jess smile. They felt the same exact way about books. Then she moved on to her second world, the real world, in which her family and friends lived. She thanked her grandparents. "I am proud to be their grandchild," she said. "And I'm thankful for another presence in my life." She searched the audience until she found Jess' face, then locked eyes with him. "The Artful Dodger." She didn't say anything else, but she didn't have to. Jess felt an unfamiliar warmth in his chest and a lump in his throat. He could sense Luke's eyes on him, so he tried his hardest to keep his facial features neutral. As Rory continued on, thanking her mother, all dams broke down and the rest of the group, even Luke, started blubbering.

"What did we agree?" Jess said to his uncle, mockingly angry. To his surprise, his voice broke a little, and, embarrassed, he covered his mouth.

"Got to you too, huh?" Jackson said, leaning across and giving Jess a manly pat on the shoulder.

"No!" Jess said insistently, even as he felt his eyes gloss over with tears. Lorelai and Sookie were both staring at him, wobbly smiles on their faces. Luke was hiding a grin too.

"He's just an old softie," Lorelai stage-whispered to Sookie, and Jess ducked his head, running his fingers through his hair.

"Your daughter's still on stage," he pointed out, his voice steadier. "Don't you want to pay attention to that?" Lorelai jumped, faced forward, and started snapping pictures. Relieved to have the attention of the group back on Rory, Jess slumped in his chair. Rory finished her speech, throwing one last glance at Jess before she left the stage, and the ceremony began.

After the ceremony ended, Jess waited with the rest of the group for Rory to come out. He watched her hug the crazy socialist Pledge of Allegiance girl – Paris, if he remembered correctly – and felt that weird lumpy thing in his throat again as she turned to him.

"Did you like my speech?" she asked shyly.

"I really did," he said, and gave her just a quick peck on the lips, since everybody was watching. "I'll show you how much later," he whispered in her ear, making her blush.

"Rory, dear, thank you for your speech," her grandfather said as they pulled apart.

"Yes, thank you," her grandmother added, both of them unabashedly teary-eyed. "Now we have something to show you, Rory." Everyone walked out to the parking lot, where at least two dozen brand-new cars with giant bows on them resided.

"It's the one with the bow on it," Richard said proudly. Everyone stared at him until he glanced around. "Oh," he said, scratching his head. "Well, it's a little Prius."

"It's the same car as Leonardo DiCaprio drives," Emily added as if this were a great selling point. Jess smiled. This would definitely make the distance between Stars Hollow and Yale – 22.8 miles; he'd looked it up – a lot easier to deal with. It was like a present for him too, but he was sure Rory's grandparents would think twice about the car if they knew that.

"Rory, come this way with me for a minute," Lorelai said after Rory had profusely thanked her grandparents. They ran off and Jess stood awkwardly with the rest of the group.

"Well, there's a celebration back at Lorelai and Rory's," Sookie said. "We might as well get going, help set some stuff up." Jackson nodded and they left, along with the grandparents, but not before Emily gave Jess a withering stare. He was sure there were many of those to come at the celebration. He sighed, remembering what Luke had said about how dating a Gilmore girl meant dating her entire family.

"Let's head out," Luke said, clapping Jess on the shoulder. "Did you like Rory's speech?" he asked in a lower tone. Jess shrugged.

"Yup," he said shortly, knowing that his crying incident was more than enough proof that he'd liked it. Luke laughed as they climbed in his truck and they spent the 30-minute ride back to Stars Hollow in silence, Jess with a stoic expression on his face, Luke unable to wipe the smirk off of his own.

**A/N: Aww. Next chapter I will get back to the prom, I promise! But I hope you enjoyed my little rewrite of Rory's graduation!**


	6. Leave the Gun, Take the Cannoli

**A/N: We're not QUITE at the prom yet, sorry to disappoint. This is a little back-and-forth I came up with, little vignettes describing Rory and Jess separately as they get ready for the prom. Hopefully you'll like it. **

**P.S. The article Lorelai mentions actually ****_is _****in ****_Cosmo_****, but obviously the movie's coming out now, not…however many years ago this would be. Ten years? Wow. Anyway, artistic license!**

Luke had been exiled from his own apartment. He was not allowed to come upstairs for cases of mustard, tools, extra ones for the cash register, or any other imaginable object he might need for the diner to run smoothly. Not today. Today, Jess was getting ready, and the last thing he wanted was his uncle standing in the corner, smirking, like he had when Jess had bought the suit. Said suit was currently hanging off the back of the bathroom door as the suit's owner showered.

"I hope I can pull this off," he mumbled as he squirted shampoo into his palms. He wasn't talking about the suit.

/

Meanwhile, at the Gilmore house, Rory was also getting ready, but Lorelai's help was more than welcome, in this case.

"Mom! I can't find my – "

"On your dresser!"

"Mom! Where's the – "

"In the cupboard, underneath the towels."

Lorelai's help was indispensible, actually. Waking up that morning, Rory had a sudden bout of uncertainty about the day to come. Jess didn't have the best track record. What if he didn't show? What if somebody started a fight? What if he hated her dress? What if all that pizza and candy and ice cream she'd consumed during the previous night's Gilmore movie marathon (_Pretty in Pink_, followed by _Valley Girl _and a quarter of _Never Been Kissed _– they'd fallen asleep before Josie even took the undercover assignment) had found its way onto her hips and the dress didn't even _fit_?

"Metabolism, don't fail me now," Rory muttered in the bathroom, turning the faucet to make the shower water extra-hot, the way she liked it.

/

A towel wrapped around his waist, Jess stood before the closet and selected the white button-down he'd bought at _not_-Walmart. "I might as well be wearing a clown suit to this thing," he muttered to himself, removing the towel and ruffling it through his damp hair. It was hot outside, too, much too hot to wear long sleeves and a _jacket_. What sadist had decided the prom had to take place in the summer? And the shoes he'd also purchased at _not_-Walmart? Didn't exactly offer a lot of air circulation. _And_ they pinched his toes, just a little.

/

"One last time, Rory – do these shoes pinch your toes? Because if so, you have to put them on now so your feet will get numb," Lorelai warned.

"That's sick," Rory said, echoing her sixteen-year old self.

"No combat boots!" Lorelai sang, exiting the room with an exaggerated point to the silver, twenties-style heels in the corner. Luckily, they weren't actually _from _the 1920s, so Rory was hopeful she wouldn't have to deal with any heel-breaking tonight. _Tonight_. The prom was tonight. And Jess was taking her. She couldn't help but smile at that. And he said he had some big surprise planned. Rory's smile degenerated into a frown. That could be good or bad…or somewhere in between.

/

Belt buckled, shoes pinching, and button-down all buttoned up, Jess stared intently at his own reflection. The bottle of gel was in his left hand, ready to shape his hair _just so_, but he was hesitating. His signature tousled, messed-up-on-purpose style hadn't exactly been a huge hit in the 20s. The rest of him had time-warped – why not his hair, too? But then again, as far as he knew, Rory liked his hair the way it was. What would _her _hair look like? "I've never felt more like a girl than in this moment," Jess deadpanned to his reflection.

/

"I just don't know how you're going to make my hair look like a flapper's," Rory said, shrugging her shoulders. She was sitting in front of the vanity in her mother's room, dressed in her favorite pink robe, staring at her own (long-haired) reflection. "It's way too long. Unless you're about to come at me with shears – " Rory turned to look as her mom reentered the room, checking for scissors. Lorelai laughed at her expression.

"No, hon, I wouldn't touch your hair with scissors. Remember the Great Haircut Disaster of '95?"

"All too well," Rory groaned, recalling the incident – Lorelai, looking to save just a few dollars, had endeavored to give eight-year old Rory a homemade haircut the day before the start of second grade. Even then, little Rory was skeptical, and begged her mom to take her to the salon. She'd even pay for it out of her own savings, she said, pulling out her piggy bank to prove it. But 24-year old Lorelai was insistent, and had the added advantage of being the mom, so Rory reluctantly sat for the haircut. Which was disastrous. She looked like Bobby Brady for a month. "You still owe me for that one."

"Well, maybe after I finish your hair, you'll forgive me. Way to hold a grudge!" Lorelai said jokingly. Rory turned back to her reflection with trepidation. "I'm just gonna need about ten trillion pins." Lorelai held up three packages of bobby pins. "Turns out Carol Channing was wrong, _bobby pins _are a girl's best friend!" she quipped. Then she set to work.

/

Having settled on a style somewhere in between the usual Jess Mariano and Michael Corleone – slick, but not _too_ slick, and minus the accompanying Italian mob – Jess flipped the matching jacket over his arm and headed down to the diner. Despite his most ardent hopes and prayers, at least half of Stars Hollow was having lunch, so there were way too many witnesses to kill. _I knew I shouldn't have watched _The Godfather_ last night_, Jess thought, avoiding the gaze of Miss Patty, Babette, Maury, East Side Tilly, Kirk, Taylor, half a dozen assorted townies, and of course, Luke. He stepped quickly, was almost to the door, but – "Damn, sugah!" Babette's gravelly voice burst through the silence and Jess winced. "You clean up good!"

Jess turned to see her and Miss Patty looking at him like he imagined wolves must look at a little lost lamb. The rest of the diner's patrons just looked bewildered, as if Jess Mariano had gone upstairs and come down an entirely different person…which to them, he supposed, he was. Even Luke was staring at him oddly, even though he'd already seen his nephew in the suit.

"Have a good time at the prom!" Miss Patty called cheerfully, and breaking the stunned silence. "Don't do anything I wouldn't do!" she added, chuckling throatily and giving him a disturbing wink that indicated there wasn't much Miss Patty wouldn't do.

"He does look like he's just stepped out of the 1920s," Jess heard somebody say from behind him as he stepped onto the street.

"He looked like he was about to rob a bank!…in the 1920s," Taylor's voice observed suspiciously. Jess couldn't help but smile at that one.

_If anything, I'd knock over a liquor store_, he mentally retorted, patting the inside pocket to make sure the flask full of whiskey was still in there, then he headed in the direction of Gypsy's.

/

"Ta-da!" Lorelai sang, beaming down at her daughter. Halfway through pinning Rory's hair up, she'd decided to turn her daughter around so she couldn't see what her hair looked like until the very end, crowing "It's just like _What Not to Wear_!" As much as Rory discouraged this very dangerous decision, Lorelai _had _made her dress…and bought her shoes…and was helping her get ready in every which way, so she couldn't, in good conscience, complain.

Her pulse speeding up, Rory bit her lip and cautiously turned the chair back the right way to face the music (and the mirror).

"Oh my god…_Mom_!" she gasped. Somehow, some way, with nothing but an excess of bobby pins and a _lot _of hairspray, Lorelai had coaxed Rory's long tresses into a flawless flapper bob. "It's perfect!" Rory exclaimed, turning this way and that to admire her reflection. "_How _did you do this?"

Lorelai shrugged. "The magic that is _Cosmo_," she replied, holding up the latest issue. "That movie version of _The Great Gatsby _is coming out soon, and they're all about the faux bob in Hollywood, apparently, and of course _Cosmo _wants you to look just like a celebrity, so…"

"I would hug you right now if I wasn't so concerned my hair would get messed up," Rory said ardently, settling for an awkward half-hug around Lorelai's waist. "You are totally and completely forgiven for the Bobby Brady hair incident."

"How are you gonna do your makeup?" Lorelai asked. "Can I help with that too?"

"Your help is not only encouraged, but required, after this," Rory said, indicating her hairdo.

"A-ha!" Lorelai said, a glint coming into her eye. She picked up the eyeliner.

"Not _too _much," Rory insisted. "I want to look like I'm going to prom, not like I'm for sale."

"Jess is gonna flip," Lorelai assured her, giving her a smile that indicated she was okay with the town rebel taking her one and only daughter to prom…at least until he did something stupid.

**A/N: Hmm…somewhat foreboding…uh-oh…**


	7. Ain't Misbehavin'

**A/N: You may notice that it seemingly took Jess three hours to get from Luke's to Rory and Lorelai's house. Hold your horses; there's an explanation. Read on!**

"So when's he picking you up?" Lorelai asked as she put the final touches on Rory's ensemble. The dress was on (it still fit perfectly, to Rory's great relief), her hair and makeup were done, and the shoes were numbing her feet as they spoke.

"The prom starts at 5, so I think he should be here soon…" she trailed off, glancing at the clock on the mantle. It was 4:30. _Not time to panic yet_, she soothed herself, trying and failing to hide any anxiety from Lorelai.

"He'll be here, hon," the older woman assured her. As if to cement her words, a knock sounded at the door. "Maybe that's him!" Lorelai said brightly. Rory stood back, nervously checking her reflection. "Mom?!" Lorelai's astounded voice came from the foyer.

"Grandma?" Rory asked, confused.

"Lorelai Victoria Gilmore!" Emily boomed. Rory winced, glad she wasn't standing closer. "How could you hide the fact that my one and _only _granddaughter is attending the prom _tonight_?"

"We didn't _mean _to hide it, Mom, I guess we just forgot to mention it," Lorelai apologized.

"'Forgot' to mention it?" Emily exclaimed, her voice hitting a high note at the end of her sentence. "You were at dinner just last night, and you _forgot _to mention it?" She walked into the living room, looking like she had a bad taste in her mouth. Then she caught sight of Rory. "Oh, _Rory_! You look absolutely enchanting! Where on earth did you buy that dress?" Emily stepped closer to her granddaughter and gave her an air hug, so as not to muss her dress.

"Very Emily Post, Mom," Lorelai said dryly. "And I made the dress."

The Gilmore matriarch pursed her lips. "You made it. Well. Lorelai, you did a nice job…again," she said, referring to Rory's Chilton dress. Then she frowned. It seemed to be her default expression. "But the Chilton prom isn't till tomorrow night," she said, turning in confusion from Rory to Lorelai.

"She's not going to the Chilton prom, Mom," Lorelai said patiently. "She's going to the Stars Hollow prom. With her boyfriend. Who attends Stars Hollow High."

"You remember, Grandma. Jess. He was at…graduation…" She trailed off nervously.

Emily stared at Lorelai, making no attempt to hide her displeasure from Rory. "You're letting her go to prom at a _public _high school with that – that – "

"That very nice guy who's been dating Rory for over six months? Yup, that one," Lorelai filled in. Rory shot her a grateful look just as another knock came at the door.

"Good timing, Jess," Lorelai muttered under her breath as she went into the foyer again. "Whoa. Rory? Come here!" she said excitedly.

"What, what?" Rory asked, hurrying to see what had caused the sudden change in Lorelai's tone. "Whoa."

Emily approached the Gilmores' door more slowly, a thousand different ideas of what could be in the yard that was so fascinating to her girls running through her head. She gasped.

A shiny white Duesenberg – Emily only knew the name because Richard had raved about one at a car show a few years ago – was pulled into the driveway behind Lorelai's Jeep, Rory's new Prius, and Emily's Mercedes. It took Emily a moment to reconcile the poorly-dressed hooligan at dinner months ago and at Rory's graduation with the man who was standing in the yard now.

"Hey," Jess said, a little taken aback. He'd been expecting just two Gilmore girls, and now he had to contend with three, all standing on the porch and staring at him. "Hi, Rory," he said more specifically, catching sight of his girlfriend, hovering slightly behind her mother. He bit his lip, trying to hold back a grin. She looked incredible.

Meanwhile, Rory was thinking the same about Jess. She hardly recognized him without the baggy jeans and moussed-up hair. She just stood there silently, her mouth open. When Jess had told her he had a big surprise for prom night, she'd been expecting, well, not this. "H-how?" she said faintly. "Where did – where did you get the car? And the suit? And the – how?"

Jess shrugged. "Called in a few favors," he said simply.

The last time Gypsy worked on Jess' beat-up old car, she'd way overcharged him for something Jess could probably have done on his own. He only discovered this after he got back to Luke's and looked at his receipt properly. He'd stomped back to Gypsy's and argued with her, largely unsuccessfully, before shouting that she owed him one. Sick of fighting for once, Gypsy reluctantly agreed. Turned out she had connections with some guy in New Canaan who collected vintage cars, and the rest was history. Then, as if that hadn't been enough, he had to convince the guy that he wouldn't get even a tiny scratch on it and would _only _put premium gas in it if it needed it. It had taken some time.

"The suit I just bought," Jess continued, a faint smile on his face. "They're pretty easy to find if you know where to look."

Rory was so stunned that she hadn't even left the porch. Lorelai put her hand on the small of her daughter's back and gave her a little push. "Go on," she urged out of the corner of her mouth. "No, wait, let me grab something. Then you can go," she amended. Meanwhile, Emily appeared to be rooted to the spot.

"I do not approve of this," she said, holding her head high and staring Jess down. He sighed.

"All due respect…ma'am…but I think Lorelai's the one who has to approve of this," he pointed out. "And I think she already has," he continued as Lorelai popped back out with a string of pearls in her hand. Emily looked stunned.

"Final touch," Lorelai whispered to her daughter, fastening the jewelry around her neck. Then she turned to her own mother. "Mom. I know you hate this. I know you're having flashbacks of the Chilton dance right now, 'cause I'm having them too." Here Lorelai glanced at Jess. "I need to give him another chance, Mom," she said more quietly. "Rory did." Emily made a _tsk _noise and turned to go back inside the house, too fed up to say much more.

"Home by eleven!" she called authoritatively.

"Twelve," Lorelai mouthed to Rory and Jess, waving goodbye and beaming at how lovely Rory looked. She bit her tongue before she could add "And be careful." She didn't need to. Rory was always careful. Jess, on the other hand…_no_, she said to herself firmly. _Just go back inside…to contend with Emily_. She heaved a long-suffering sigh and closed the door behind her.

"So…do you like it?" Jess asked, opening the passenger door for Rory.

"Jess, it's _amazing_. I can't even – I don't have words," she said helplessly, stepping into the car.

He laughed as he shut the door behind her and went to open his own. "That's a first."

"Shut up," she said good-naturedly.

"She found her vocabulary again! It's a miracle!" Jess exclaimed.

Rory giggled. "Just drive, Jeeves."

"Seatbelts on?" Jess asked, a mock-stern expression on his face. Rory nodded, returning his serious gaze. He leaned over as if to check if her belt was secure, sneaking a hand on her shoulder and pulling her to him for a kiss. "You look amazing," he whispered, making her blush.

"So do you," she said back quietly. "Seriously, where'd you get the suit?"

"That ancient Italian place at the end of Plum," he replied, pulling back and starting the engine. "The guy tried to sell me a fedora, too."

"Oh, you should have worn one!" Rory cried.

"So every other guy at the prom would beat me up? No, thank you," Jess said, looking to the left and right before turning. "So why's your bag so massive?" he asked, glancing at the sack she held on her lap.

"There's not that much in it," Rory defended. "A lipstick. Extra bobby pins. Hairspray. A book."

"A book?" Jess asked. "You expecting a lot of downtime at this thing?"

Rory laughed. "No, I just take a book with me everywhere."

"I know," Jess replied, smiling a bit. "So do I." He gestured to the floor, near Rory's feet. A worn-looking copy of _The Great Gatsby _resided there. "I just finished it. What'd you bring?"

Rory just grinned and held up her own copy of the same exact book.

"Huh. Interesting," Jess said.

"One would think we have similar tastes or something," Rory shrugged, unable to wipe the smile off her face. "Oh, I hope this isn't too lame," she said wistfully as they pulled into the parking lot behind the high school.

"Well, only one way to find out," Jess replied, shifting the car's gears into _park_ and trying not to show how nervous he was.

**A/N: I hope you liked this chapter! If you want to get an idea of what the car looks like, there's a Flickr link in my profile.**


	8. Let's Dance

**A/N: I have a bone to pick with you guys. None of you corrected me about Lane and Dave – they ****_did _****get to go to prom together; that bit had totally slipped my mind, which is terrible, because it's a great scene in "Say Goodnight, Gracie." You have to catch me on these things! Okay, onto the story. :) **

"Oh, here, I forgot to give this to you," Jess said as they climbed out of the borrowed Duesenberg. He pulled a plastic container out of the narrow backseat.

"Oh, it's pretty," Rory said in a hushed tone, taking out the pale pink corsage and slipping it onto her wrist. "You didn't have to get me one."

Jess shrugged and helped her step out of the low-slung car. "Don't those heels hurt?" he asked, frowning at Rory's feet as she clung to him for balance.

"Pain is beauty, my friend," Rory assured him.

"Sure," he replied shortly. He'd rather see her comfortable in jeans and a sweater, but then again, he wasn't exactly in his element either. He tugged at his collar. Jess felt more uneasy than he cared to admit. He had never been one for school functions, whether back in New York or here. His best idea of what the actual prom might be like was gleaned from a late-night viewing of _Pretty in Pink_. "We'll leave if it's lame, right?" he asked Rory. She nodded, but he thought he saw a glimmer of disappointment in her eyes. It made him want to bolt. _Jess Mariano, disappointing people since 1985_,he thought, gripping Rory's hand tightly to prevent himself from turning around.

They made their way into the gym amongst a few other time-warped couples. Rory said hi to a couple of girls she remembered from her time at the school. Both of them gave Jess sidelong glances, as if to say 'What are you doing with _him_?' Rory never let go of his hand, for which Jess was thankful. They had to duck slightly to get through the streamers Sandy had insisted on hanging over the gym doors – "For ambiance," she'd said authoritatively – then they were inside.

"Oh my god. Wow!" Rory said, her eyes widening. Jess smiled a little, glancing around at all the work he and the rest of the prom committee had put into the decorations.

The ordinarily-beige walls of the gym were draped with deep blue fabric. A crisp white tablecloth covered every table; bottles of sparkling cider sat in an ice bucket nearby (Jess had gunned for real champagne, but Mr. Carraway, unsurprisingly, shot that down quickly). Enlarged pictures of F. Scott Fitzgerald and Zelda Fitzgerald were hanging off the basketball hoops (Jess wished he could have gotten rid of them; they really ruined the '20s feel he was going for, but there was nothing he could do about it). Dr. T.J. Eckleburg's eyes peered out from the far wall, along with a mysterious green glow (really it was a green light bulb hooked up behind one of the swatches of fabric). Jess and Mr. Carraway had combined their music collections to come up with a master mix of classic '20s tunes and some more modern stuff. A Benny Goodman song ended as they made their way to the center of the room, followed up by Tom Waits, to Rory's delight.

"Here you go, guys," Sandy said cheerfully, approaching them with the faux pearls in her hand. She was dressed in a short red fringe dress and a feather was tucked into her hair. "Thanks, Jess," she added before walking away.

"Why did she thank you?" Rory asked, handing off the plastic necklace to someone nearby. She had her mom's real ones.

Jess shrugged. "I guess she mistook me for somebody else." Rory frowned, but didn't push the subject. He had planned on telling her that he was part of the reason the room looked so good, but once they were there, he just felt kind of embarrassed. _Maybe this was all too much_, he thought regretfully. There was the car, and the suit, and now all the decorations. Why had he gone through so much trouble? Jess glanced at Rory, who was smiling brilliantly, still gazing around at the transformed room. _Well. That's why_, he thought, shaking his head a little at himself.

"Rory!" Lane was waving at them from a table a few feet away. "I saved you guys seats!" she said. "Wow. You look great. Both of you." Jess was starting to get used to everyone looking at him like he had two heads, just because he was dressed in a suit and wearing his hair a little bit differently.

"You guys look great too!" Rory gushed, giving Lane a hug and waving at Dave. Although Lane's black dress was significantly longer than Rory's, it was still stylish and fit in with the flapper theme. Dave was dressed in a simple black suit.

"Hey," Jess said, nodding at Dave and Lane.

"Everyone's been talking about this car that just pulled up," Lane said confidentially, leaning in so Rory and Jess could hear her. "Apparently it's really fancy and no one knows who was in it. It's just sitting out there in the parking lot." A smile played across Rory's face, but she glanced at Jess to make sure it was okay to tell Lane. He nodded.

"Jess called in a favor with Gypsy," Rory announced. "We were in the car." She beamed proudly.

"Oh wow, um, wow!" Lane said, her surprise very thinly veiled. Jess shrugged. Lane was glancing back and forth from him to Rory, a suspicious look on her face, but she said nothing further. The beginning strains of "Let's Dance" filled the room and Rory looked at Jess.

"You promised!" she said teasingly, standing up and grabbing his hand. Jess rolled his eyes and resisted Rory's pull a little, but eventually gave in, as she knew he would.

"I knew I'd regret that," he said, allowing himself to be pulled onto the dance floor. In truth, he'd made sure that at least one Bowie song was queued up for the night's music. He could stand dancing for one song, right? His thoughts started to drift even as Rory started dancing in front of him in her cute, slightly awkward way. The Bowie reminded him of his father. Yesterday Jess had bought a plane ticket to California. It was one-way. He had no idea whether Jimmy would let him crash or kick him out immediately, and Jess didn't relish the idea of sleeping on a bench or the beach until his flight home. _Home_. He realized that he had never called Stars Hollow home before. New York was always home.

"Hey, you have to _move_," Rory said, grabbing his hands and swinging them a little. She smiled at him and he knew he couldn't just leave, even if she was going to be in Europe anyway.

"Can I talk to you for a sec?" he asked. Her smile faded and she nodded. "Not here," he added. "Let's go back out to the car." He led her out of the gym, not noticing that Dean stood by the exit, watching them.

"Jess, what's wrong?" Rory asked urgently as soon as they were outside. "Do you want to leave?"

Jess shook his head. "No, it's fine, I just…needed to tell you something." Rory raised her eyebrows expectantly. "Um…you're going to Europe next week, right?" he asked, even though he already knew the answer. "So…I kind of thought I would take a trip too. While you're gone."

"Where do you want to go?" Rory asked, looking confused. "New York?"

He shook his head again. "California."

"Well, cowabunga, dude?" Rory laughed. "I can't really picture you there. San Francisco, maybe." She waited for him to explain.

"My dad lives there," he said reluctantly. "He showed up last week, in the diner, and I just…I mean, I never knew him, so." Jess looked at his feet and kicked a nonexistent pebble.

"I think that's great," Rory said sincerely, reaching out and rubbing his arm. "If you want to get to know your dad, go do it. Even if my dad and I don't always get along, I'm still glad he stayed in touch after I was born."

_Why was I even nervous about telling her? _Jess thought, shaking his head. He'd almost forgotten that her father was absent much of the time, too. He leaned forward and kissed Rory on the cheek.

"Let's go back inside," she suggested. "I bet they play another Bowie song so we can finish that dance." Jess fake-groaned. Rory just laughed and pulled him back inside.

**A/N: Review! Review! I hope I made it sound good even if you haven't read****_ The Great Gatsby_****. And if you HAVE read it, I hope I did it justice. I wish my prom had been that cool.**


	9. The Tempest

**A/N: This is a really short chapter, but hopefully it will sustain you until I can update again.**

As soon as Jess and Rory returned to the prom, hand-in-hand, Dean strode right up to them and glowered at Jess. He was wearing a white suit and actually did have a matching fedora on his head.

"You're doing that tall thing again," Jess said calmly, staring up at Dean, who had to have been a good five inches taller – seven if you counted the fedora.

"Rory, is everything okay?" Dean asked, ignoring Jess. Lindsay crept up behind Dean, taking his arm possessively. She was wearing a close-fitting purple dress that looked more like it belonged in the seventies. Rory rolled her eyes. She had no plans to steal Dean away from Lindsay, but she knew the other girl wouldn't believe her, even if she told her so.

"Everything's fine," Rory said firmly, smiling at Jess. Dean's face crumpled a little, but almost before Rory could notice, he looked serious again.

"Are you sure he isn't bothering you?" he asked, even as Lindsay tugged gently on his sleeve, trying to persuade him to return to the dance floor.

Rory frowned. "He's my _boyfriend_," she said. "Of course he isn't bothering me."

"You got a problem with that?" Jess asked, still calm, still staring up at Dean.

"Maybe I do," he said, and Rory's stomach dropped as he reached out and pushed Jess, just lightly, but definitely enough to incite his wrath.

"Dean, _don't_," Rory said, holding onto Jess' arm so he wouldn't retaliate. She could feel him tensing up underneath his suit jacket. His head turned suddenly and she followed his gaze to Mr. Carraway, who was standing a few feet away, giving Jess and Dean a warning look. Dean looked over too.

"Forget it," he mumbled. "You're not worth the trouble, anyway." He grabbed Lindsay's hand protectively and pulled her over to the snack table. Rory breathed a sigh of relief. She did not need a repeat of Kyle's party.

"You okay?" she asked Jess. He nodded, still staring after Dean and Lindsay.

"He's an ass," he muttered.

"He just worries about me, I guess," Rory shrugged. "Not that he _needs _to," she added quickly at the look on Jess' face.

"He shouldn't worry about you," Jess replied, his annoyance coming through clearly in his tone. "_I _should worry about you. I can't believe he pushed me." His brow furrowed. He clearly wanted to retaliate, and under any other circumstances he would have, but he wouldn't ruin the prom for Rory. He _couldn't_. "Do you want to leave soon?" he asked.

She bit her lip and shrugged. "We've only been here an hour…" she said tentatively. _Is she afraid to tell me what she really thinks? _Jess thought with mild horror. What had he done to make her look at him this way, as someone she couldn't necessarily trust or confide in? His face felt hot with shame. If he was honest, it wasn't exactly like he confided in her all the time. Telling her he wanted to go to California to see Jimmy was probably the most honest he'd ever been since the night of the Dance Marathon.

"Let's stay," he said firmly, and Rory smiled. "Just…stay away from Dean." She nodded. "I'll be right back. Bathroom," he mumbled. He watched as she made her way back to their table, smiling at Lane. Pushing open the gym door, Jess hung a left, away from the bathrooms. He jiggled at door handles until he found one that opened, his math classroom. Slumping down in the teacher's chair, Jess pulled out his flask, and stared at it. Then he took a swig.


	10. Bridge Over Troubled Water

Jess didn't know how much time passed before he left the classroom. A guilty tug in his lower abdomen assured him that it had been too long. He stopped next to the entrance to the gym, tucking the empty flask back inside his jacket. He stood there for a moment. Rory would be able to tell he'd been drinking. Mr. Carraway would be able to tell too. Jess grimaced and turned away from the door. If he'd already destroyed everything, what was the harm if he left now?

The town square was unusually deserted. Not even Miss Patty's late-night yoga class was downward-dogging near the edge of Peach Street. The moon was almost full; it was bright enough to see without a flashlight. His feet knew where to go without having to tell them. He sat down, the wooden planks feeling more unforgiving than usual without his customary back-pocket book. His fingers patted around automatically for his cigarettes before he remembered that he'd quit after he and Rory started dating. The tips of his shiny black shoes drifted dangerously close to the murky water below.

"I thought I might find you here." Jess looked up. Of course she'd find him here. Hadn't he come here because he knew she'd find him? Rory carefully sat down next to him, taking care not to tear her dress on the rough wood. Her left leg pressed against his right. For a moment, they were both silent, both staring down into the water in which they could just barely make out their reflections. Neither of them looked at the other. "Why did you leave?" Rory asked, and Jess' head jerked up at how broken her voice sounded. She wasn't crying, but her lips were trembling.

"I needed some air," Jess said hoarsely. He knew she would be able to smell the whiskey on his breath.

"You needed air for an hour?" Rory asked, not making eye contact. Jess winced. Had it really been that long? He'd only planned to do a shot or two in the classroom, then head back to the dance. Dark thoughts had overtaken him, though, while he sat behind the desk, playing the part of 'teacher.' He wasn't fit to teach anybody anything. "I looked for you everywhere," she added, and his stomach sank further at the thought of Rory running around, asking people if they'd seen him. He was just fulfilling everyone's expectations.

"Is it over?" he asked. The double-meaning in his words wasn't intentional, but his breath caught in his throat as he imagined the responses she could give.

Instead, Rory just shrugged. "A lot of people are still there," she offered. So she'd chosen to take his words at face value. Then: "Jess, what's wrong? Please tell me." She finally looked straight at him and grabbed one of his hands. "You never tell me." The corners of her lips turned downwards and he felt an ache in his chest. He could never make her happy. She'd always been happy with Dean.

"Go find Dean," Jess muttered, ignoring the tear of pain that shot through him as he said the words. He snuck a look at Rory out of the corner of his eye and winced inwardly. She looked like he'd slapped her. But she stood her ground.

"Why would I want to find _Dean_?" she shot back at him, angry now. Her hands were clenched into fists in her lap. Jess watched the moonlight bouncing off the endless glitter on her dress and the gloss of tears in her eyes. He swallowed hard, his Adam's apple bobbing, and stood up. The whiskey had affected him more than he realized, probably because he'd missed dinner, and he almost lost his balance. His hand shot out and automatically grabbed onto Rory's shoulder. She hadn't been expecting all of Jess' weight to land on her and she tipped sideways. _Not again_, Jess thought before they both hit the water with a splash.

Jess kept his eyes tightly shut. Who knew what sort of dirt and grime was in this pond? His heavy suit weighted him down, but he was able to fight his way to the surface without too much trouble. "Rory?" he called as soon as he refilled his lungs with air. "Rory?" He glanced about desperately. Did she know how to swim? Then she heard her peal of laughter and whipped around, his hair flipping water droplets into the air. She was bobbing behind him, her hair completely ruined, her eye makeup running all over her face. And she was cracking up. "Rory?" Jess said once more, now slightly concerned for her sanity.

She reached out her arms and grabbed him. "Bet you're sobered up now, huh?" she asked, a huge, delighted smile on her face. Her wet hair reminded him of the day she hadn't been able to turn off the sprinklers in that weird neighbor's yard. Dean had come to her rescue that day, too, he remembered dejectedly. As if she knew what he was thinking, Rory continued, "I was gonna say…why would I want to find Dean? I came to find _you_. Why do you always think I don't want you?" she asked, cocking her head at him curiously.

_Because nobody ever has_, Jess thought. Then, almost before he realized what was happening, he said it out loud, too. "Because nobody ever has." His shoulders came up almost to meet his ears and he self-consciously pushed his wet hair back. To his surprise, Rory didn't give him that pitying look he was so accustomed to. That look was why he'd stopped saying things like "Because nobody ever has" and why he'd started using sarcasm as a defense mechanism. He could remember how shocked Liz was the first time he'd ever talked back to her, when he was nine. Rory just looked at him in that particular _Rory _way of hers – not pitying, not resentful, not judgmental – and grabbed his hand.

"We should probably get out of the water," she said. He allowed her to lead him onto the shore, which was really just a thick strip of mud. Her shoes caught in the sticky muck, so he slipped an arm behind her back and lifted her. She gasped, but allowed him to carry her the few steps back to the bridge, where he deposited her gently. Her arms immediately wrapped around herself. She was shivering, despite the humid June air. "Can we go to Luke's?" she ventured, knowing he'd prefer that to returning to the dance.

"Are you sure?" Jess asked. He was more than certain that he'd already ruined her prom an hour ago, but he wouldn't pass up the opportunity to possibly fix it. He was always trying and failing to fix things. Luke was Mr. Fix-It. Jess was just…Mr. _Try_-to-Fix-It. Rory nodded, smiling, and took his hand before they made their way back to the town square, Jess' shoes squelching with every step. "Told you I'd end up face-down in a pool," he muttered.

"Come on, Gatsby, at least your Daisy's still here," Rory replied, and he couldn't help giving her a small smile.

**A/N: And there you have it! Read and review!**

**I might try to do a little sequel - maybe just a one-shot - where Rory goes to Europe and Jess goes to California, and how they stay in touch during that time, but this is it for now. **


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